Method for producing oxide

Abstract

Provided is a method of oxidizing a substrate with excellent oxidizing power to yield a corresponding oxide. The method can employ a commercially available imide compound as intact as a catalyst and can produce the oxide in a high yield under mild conditions. A method for producing an oxide according to the present invention includes performing oxidation of a substrate in the presence of oxygen and ozone under catalysis of an imide compound to yield a corresponding oxide. The imide compound has a cyclic imide skeleton represented by Formula (I). In the formula, n is selected from 0 and 1; and X is selected from an oxygen atom and an —OR group, where R is selected from hydrogen and a hydroxy-protecting group.

The invention claimed is: 
     
       1. A method for producing an oxide, the method comprising
 performing oxidation of a substrate (A) in the presence of oxygen and ozone under catalysis of an imide compound to yield the corresponding oxide, the imide compound containing a cyclic imide skeleton represented by Formula (I): 
 
       
         
           
           
               
               
           
         
       
       wherein n is selected from 0 and 1; and X is selected from an oxygen atom and an —OR group, where R is selected from hydrogen and a hydroxy-protecting group,
 the substrate (A) including a compound selected from the group consisting of: 
 (A1) compounds containing a heteroatom and a carbon-hydrogen bond at an adjacent position to the heteroatom; 
 (A2) compounds containing a carbon-heteroatom double bond; 
 (A3) compounds containing a methine carbon atom; 
 (A4) compounds containing an unsaturated bond and a carbon-hydrogen bond at an adjacent position to the unsaturated bond; 
 (A5) alicyclic compounds; 
 (A6) conjugated compounds; 
 (A7) amine compounds; 
 (A8) aromatic compounds; 
 (A9) normal alkanes; and 
 (A10) olefins. 
 
     
     
       2. The method according to  claim 1  for producing an oxide,
 wherein a metallic compound is used as a promoter in combination with the imide compound as a catalyst. 
 
     
     
       3. The method according to  claim 2  for producing an oxide,
 wherein the metallic compound includes at least one metal element selected from the group consisting of cobalt, manganese, zirconium, and molybdenum. 
 
     
     
       4. The method according to  claim 1  for producing an oxide,
 wherein the oxidation as a reaction is performed using approximately no solvent. 
 
     
     
       5. The method according to  claim 1  for producing an oxide,
 wherein the oxidation as a reaction is performed under normal atmospheric pressure. 
 
     
     
       6. The method according to  claim 1  for producing an oxide,
 wherein the oxidation as a reaction is performed in the presence of at least one selected from the group consisting of nitric acid and nitrogen oxides. 
 
     
     
       7. The method according to  claim 1  for producing an oxide,
 wherein the oxidation as a reaction is performed at a temperature of 100° C. or lower. 
 
     
     
       8. A method for oxidizing a substrate, the method comprising
 oxidizing a substrate (A) in the presence of oxygen and ozone under catalysis of an imide compound, the imide compound containing a cyclic imide skeleton represented by Formula (I): 
 
       
         
           
           
               
               
           
         
       
       wherein n is selected from 0 and 1; and X is selected from an oxygen atom and an —OR group, where R is selected from hydrogen and a hydroxy-protecting group,
 the substrate (A) including a compound selected from the group consisting of: 
 (A1) compounds containing a heteroatom and a carbon-hydrogen bond at an adjacent position to the heteroatom; 
 (A2) compounds containing a carbon-heteroatom double bond; 
 (A3) compounds containing a methine carbon atom; 
 (A4) compounds containing an unsaturated bond and a carbon-hydrogen bond at an adjacent position to the unsaturated bond; 
 (A5) alicyclic compounds; 
 (A6) conjugated compounds; 
 (A7) amine compounds; 
 (A8) aromatic compounds; 
 (A9) normal alkanes; and 
 (A10) olefins. 
 
     
     
       9. An oxidation reaction apparatus comprising a reactor for oxidizing a substrate (A) in the presence of oxygen and ozone under catalysis of an imide compound containing a cyclic imide skeleton represented by Formula (I): 
       
         
           
           
               
               
           
         
       
       wherein n is selected from 0 and 1; and X is selected from an oxygen atom and an —OR group, where R is selected from hydrogen and a hydroxy-protecting group,
 the substrate (A) including a compound selected from the group consisting of: 
 (A1) compounds containing a heteroatom and a carbon-hydrogen bond at an adjacent position to the heteroatom; 
 (A2) compounds containing a carbon-heteroatom double bond; 
 (A3) compounds containing a methine carbon atom; 
 (A4) compounds containing an unsaturated bond and a carbon-hydrogen bond at an adjacent position to the unsaturated bond; 
 (A5) alicyclic compounds; 
 (A6) conjugated compounds; 
 (A7) amine compounds; 
 (A8) aromatic compounds; 
 (A9) normal alkanes; and 
 (A10) olefins. 
 
     
     
       10. The method according to  claim 2  for producing an oxide,
 wherein the oxidation as a reaction is performed using approximately no solvent. 
 
     
     
       11. The method according to  claim 3  for producing an oxide,
 wherein the oxidation as a reaction is performed using approximately no solvent. 
 
     
     
       12. The method according to  claim 2  for producing an oxide,
 wherein the oxidation as a reaction is performed under normal atmospheric pressure. 
 
     
     
       13. The method according to  claim 3  for producing an oxide,
 wherein the oxidation as a reaction is performed under normal atmospheric pressure. 
 
     
     
       14. The method according to  claim 4  for producing an oxide,
 wherein the oxidation as a reaction is performed under normal atmospheric pressure. 
 
     
     
       15. The method according to  claim 10  for producing an oxide,
 wherein the oxidation as a reaction is performed under normal atmospheric pressure. 
 
     
     
       16. The method according to  claim 11  for producing an oxide,
 wherein the oxidation as a reaction is performed under normal atmospheric pressure. 
 
     
     
       17. The method according to  claim 2  for producing an oxide,
 wherein the oxidation as a reaction is performed in the presence of at least one selected from the group consisting of nitric acid and nitrogen oxides. 
 
     
     
       18. The method according to  claim 3  for producing an oxide,
 wherein the oxidation as a reaction is performed in the presence of at least one selected from the group consisting of nitric acid and nitrogen oxides. 
 
     
     
       19. The method according to  claim 4  for producing an oxide,
 wherein the oxidation as a reaction is performed in the presence of at least one selected from the group consisting of nitric acid and nitrogen oxides. 
 
     
     
       20. The method according to  claim 5  for producing an oxide,
 wherein the oxidation as a reaction is performed in the presence of at least one selected from the group consisting of nitric acid and nitrogen oxides.